My first shoes

No, it's not like I have never owned shoes. It's that I never gave shoes (or clothes in general) much thought. Allow me to explain.

A brief history: I used to be the king of guy who would buy the best looking shoe for way under $100. That's it.
And as you can probably guess, sometimes I hit it out of the park, and sometimes I didn't. So I decided to change. I decided to upgrade my wardrobe, starting with my shoes, the area most in need of an upgrade (as in: I don't have any shoes).

So, I want quality and after reading lots of blogs, I've come up with a starter list. I don't think I can afford to buy them all at the same time, but I would at least like to buy two, one black and one brown. Fell free to comment on my list and give me strategies about it. I am not nearly as experienced as you guys are. I'll give you examples of what I want whenever possible. I don't want rubber soles--they look too casual to me. I prefer leather soles.

1. Black cap toe (ex.: like this one from Alden.)
2. Brown wing tip (ex.: ahhh, if only money were no issue, I'd buy this Peal & Co. I even posted a question about this particular shoe.)
3. Black split toe (I'm following a thread on split toes and I asked for a recommendation there.)
4. Brown plain toe derby (ex.: this Carmina shoe would do the trick, but it's too light. I'm looking for chocolate brown.)

What do you think? I would like to buy them in the order I posted, but if there are any deals out there that I should take advantage of, I have no problem buying out of order.

Thanks.

My first shoes